“Someone stole all my credit cards, but I won’t be reporting it. The thief spends less than my wife did.” (Henny Youngman)  

I don’t envy the women of Generation Z when it comes to the prevailing dating scene.  For this younger generation, the lines on the playing field are frequently moved, leaving those who are slow to acclimate feeling perplexed.  TikTok has become the soapbox for expressing dating busts heightened by unrealistic expectations and communication fails. Chivalry is suppressed, feminism is confused, and traditional gender roles have flown right out the window.   

The male lead in picking up a check is no longer considered a flex in profeminist circles and with disgruntled men who have felt ignored and spurned for too long.  Economic equality has created a sort of unwelcome ambiguity as to who steers the direction of the date, with a diminished patriarchy still desirous of being noticed.  It’s not a wonder that the current trend of a “sex recession” seems to be in full swing; studies confirm that Millennials and Gen Z are less partnered up than previous generations of the same age.  Dating apparently has become a minefield, replete with a blindfold and a cigarette.  

The Boomers of my generation had it easier when it came to dating.  Traditional roles were still intact. It was acceptable for a woman to flirt like a spotted hyena with fluttering eyelashes, but the expectation remained that the man ask for the first date. And the man was expected to pay. If a woman was interested, the cost of the date didn’t matter if it felt aligned with his lifestyle.  Men weren’t expected to spend money that was allotted for more pragmatic things such living expenses, that would appear to be unreasonable and selfish.  

Yet, there was always the cheapskate lurking behind the curtain. It’s worth noting the distinguishable difference between a cheapskate and a person who is respectful of their budget, with words unnecessary to define.  Women of my generation knew who they were.  The distinct aroma that follows a cheapskate is like a mix of paint thinner and pickle juice.  It’s a pungency that can’t be ignored.  

Ergo, I give you the “The Three Bears of Spenders” from the dating archives:  

BEAR #1 was the quintessential Big Spender.  His wallet entered the room before he did; his Platinum card within easy reach, nestled in buttery soft leather that was embossed with a thumbprint from consistent reach. Bear #1 was the first in his family to make significant financial gain, and he didn’t hesitate to make up for lost time.  Spending was his passage into the world and into romance, with each bottle of Cristal champagne announcing that he’d arrived.  I can’t deny that a night out with him wasn’t fun, it was, but as with many men who succumb to swashbuckler spending, his lack of temperance didn’t stop with money. Imprudence became a wary personality trait.    

Being on a date with Bear #1 could be exhilarating and unsettling.  At times his extravagance felt as though you were a kid at Disneyland with an unlimited pass, enjoying one thrilling ride to the next, yet an uneasy feeling accompanied any given moment, as if a security guard could materialize from behind Mr. Toad’s Wild Ride to detain you for a crime you didn’t commit. It came as no surprise to me years later when I read that Bear #1, who apparently had been living the life of a substandard Bernie Madoff impersonator, was indicted for financial fraud.  

BEAR #2 was the ultimate cheapskate; he could have given Jack Benny a run for his money. Bear #2 was a man of means; a successful business owner in his own right with assets, real estate equity and no dependents tugging at his purse strings, yet his approach to spending was tighter than a Quahog clam shell.  A date with him felt ill at ease and crimped, much like a pair of high heels that are ripped off immediately upon returning home.  The unpaid expenditure of the date became an elephant in the room with a dollar sign stamped on its hide.  When he questioned our waiter as to a discrepancy charge of $1 on the cost of an item on the check, the hairs on my forearm stood upright in embarrassment and tried to convince me to take refuge in the ladies’ room. His penny-pinching overrode any joy to be seized in the moment.   

It wouldn’t have mattered if he were as handsome Pierce Brosnan or as charming as the Dos Equis man.  The moths that flew from his wallet communicated that a president’s face on a greenback was more valuable than the pleasure of your company.  Being a skinflint when you’ve been blessed with ample assets is the ultimate in a can of romance repellant to most women, yet sadly for him it remained an unrealized truth.

BEAR #3 was the ultimate in dating comfort.  A confident man who took the financial lead in a relaxed manner that felt respectful and balanced.  Money was not used as a power play nor a statement; it remained in the background to enjoy time spent together in whatever capacity was called upon.  Bear #3’s make it easy and effortless to enjoy time spent together.

In the end, it’s not about dollars and cents.  Generosity and stinginess are a spirit that surpasses any financial exchange.  It’s a way of interacting with the world and with others.  It can be as simple as paying for a cup of coffee at a Starbuck’s register without expectation. An uncomplicated act that says I’m happy to be with you. A simple bouquet of flowers can express a thank you greater than a more extravagant price tag. 

As with most things in life, it’s the intention that fuels the action.